Former Trump national security adviser John Bolton is expected to plead guilty in a federal case involving allegations that he improperly handled national defense information contained in personal diary entries, marking a major turning point in a long-running legal dispute over how sensitive government-related material was retained and used.

Bolton is scheduled to enter his plea at a rearraignment hearing set for June 26. Under the agreement, he will plead guilty to a single count of retention of national security information, a significant reduction from the 18-count indictment originally brought under the Espionage Act when he was charged in October. The earlier charges stemmed from allegations that he mishandled and retained sensitive information while preparing materials connected to a potential memoir.

As part of the resolution, Bolton has agreed to pay $2.25 million. The plea deal also limits potential incarceration, ensuring that any prison sentence would not exceed five years. His legal team is expected to argue for no prison time at all, though sentencing ultimately rests with the court following any recommendation from federal prosecutors.

The case is being overseen by Theodore Chuang, who will determine whether to accept the plea agreement and later impose sentencing. The proceedings place significant discretion in his hands, particularly given the reduced charge and the high-profile nature of the case.

According to individuals familiar with the investigation, the allegations center on more than a thousand pages of diary-style entries that Bolton allegedly shared with two family members while assembling material for a potential book. Prosecutors argue that the entries contained references to national defense information that should not have been retained outside approved government systems or incorporated into personal records.

The case does not allege that Bolton physically removed classified documents from secure facilities. Instead, it focuses on whether sensitive national security information was improperly recorded, stored, and shared in personal notes. Those notes were reportedly shared only with his wife and daughter during the drafting process of his memoir, according to sources familiar with the matter.

Supporters of Bolton have pointed to prior federal cases involving former officials such as Sandy Berger and David Petraeus, noting that similar misconduct allegations have sometimes resulted in penalties that did not include incarceration. However, violations involving national defense information are prosecuted seriously under federal law, and sentencing outcomes have varied widely depending on intent, harm, and handling of classified material.

Coverage of the plea agreement was first reported by CNN.

Bolton has long maintained that he is the target of political retaliation. His relationship with current U.S. leadership has been strained for years. He was dismissed from his role during President Donald Trump’s first term and has remained one of the most prominent critics of Trump’s foreign policy approach. In turn, Trump has frequently criticized Bolton in public statements, contributing to a deeply adversarial dynamic between the two.

The case has moved slowly through pretrial stages as attorneys debated the handling of sensitive materials and classification issues tied to discovery. Bolton is not currently scheduled to file additional pretrial motions until July, but the upcoming plea hearing is expected to significantly reshape the trajectory of the case.

With the agreement in place, attention will now shift to how Judge Chuang evaluates the facts, the reduced charge, and competing arguments over sentencing. The outcome may also influence how future cases involving personal recordkeeping and national security information are prosecuted in federal court.